A full-forward, Kingsley was recruited from South Australian National Football League (SANFL) club Woodville-West Torrens along with his twin brother Wade by Port Adelaide, but the brothers were quickly traded to North Melbourne for Paul Geister in 1996.
During 2006, Kingsley was dropped from the side midway through the season despite the Cats' lack of other forward options.
He played only three senior games in 2007 for Richmond, and he announced his retirement from AFL football on 28 August 2007.
The same year, Kingsley made his AFL debut playing for North Melbourne at the age of 21.
Off the field, Kingsley has worked as an internet entrepreneur and co-owned a Geelong-based restaurant with fellow Geelong footballers Steven King and Matthew Scarlett called the George and Dragon Hotel from 2004 to 2007, until it changed name and ownership due to financial difficulty.